CA1337528C - Methode de preparation de derives de l'acide pyrazolecarboxylique - Google Patents

Methode de preparation de derives de l'acide pyrazolecarboxylique

Info

Publication number: CA1337528C
Authority: CA; Canada
Prior art keywords: compound; preparing; group; manganese; cobalt
Prior art date: 1988-07-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA000604241A

Other languages

English (en)

Inventor

Shinichiro Takigawa

Shuzo Shinke

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nissan Chemical Corp

Original Assignee

Nissan Chemical Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-07-04

Filing date

1989-06-28

Publication date

1995-11-07

1989-06-28 Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp

1995-11-07 Application granted granted Critical

1995-11-07 Publication of CA1337528C publication Critical patent/CA1337528C/fr

2012-11-07 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 title claims abstract description 31
238000000034 method Methods 0.000 title claims description 33
-1 pyrazole compound Chemical class 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
150000002736 metal compounds Chemical class 0.000 claims abstract description 11
239000003054 catalyst Substances 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
239000007789 gas Substances 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
COLOHWPRNRVWPI-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound [CH2]C(F)(F)F COLOHWPRNRVWPI-UHFFFAOYSA-N 0.000 claims abstract description 3
101100006370 Arabidopsis thaliana CHX2 gene Proteins 0.000 claims abstract description 3
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims abstract description 3
108010081348 HRT1 protein Hairy Proteins 0.000 claims abstract description 3
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
230000001590 oxidative effect Effects 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
238000004519 manufacturing process Methods 0.000 claims abstract 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 26
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
125000001931 aliphatic group Chemical group 0.000 claims description 10
229940011182 cobalt acetate Drugs 0.000 claims description 10
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 10
229940071125 manganese acetate Drugs 0.000 claims description 10
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
CIWULABPOIGMEU-UHFFFAOYSA-N 3,5-dichloro-1,4-dimethylpyrazole Chemical compound CC=1C(Cl)=NN(C)C=1Cl CIWULABPOIGMEU-UHFFFAOYSA-N 0.000 claims description 8
239000013522 chelant Chemical class 0.000 claims description 8
229910017052 cobalt Inorganic materials 0.000 claims description 8
239000010941 cobalt Substances 0.000 claims description 8
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 5
229910052748 manganese Inorganic materials 0.000 claims description 5
239000011572 manganese Substances 0.000 claims description 5
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
150000001868 cobalt Chemical class 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
229910001882 dioxygen Inorganic materials 0.000 claims description 4
150000002696 manganese Chemical class 0.000 claims description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 4
LGTRXZPAYGKNLP-UHFFFAOYSA-N 1,5-dimethyl-3-(trifluoromethyl)pyrazole Chemical compound CC1=CC(C(F)(F)F)=NN1C LGTRXZPAYGKNLP-UHFFFAOYSA-N 0.000 claims description 3
WYLLIHCCRZGVSG-UHFFFAOYSA-N 5-chloro-1,4-dimethylpyrazole Chemical compound CC=1C=NN(C)C=1Cl WYLLIHCCRZGVSG-UHFFFAOYSA-N 0.000 claims description 3
IRZUPNLPCUWKMN-UHFFFAOYSA-N 5-chloro-2,4-dimethylpyrazole-3-sulfonamide Chemical compound CC=1C(Cl)=NN(C)C=1S(N)(=O)=O IRZUPNLPCUWKMN-UHFFFAOYSA-N 0.000 claims description 3
MTTYMYCXFQTJQS-UHFFFAOYSA-N 5-tert-butylsulfanyl-3-chloro-1,4-dimethylpyrazole Chemical compound CC=1C(Cl)=NN(C)C=1SC(C)(C)C MTTYMYCXFQTJQS-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 3
150000002506 iron compounds Chemical class 0.000 claims description 3
HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 claims description 2
SZQCPPRPWDXLMM-UHFFFAOYSA-N 1,4-dimethylpyrazole Chemical compound CC=1C=NN(C)C=1 SZQCPPRPWDXLMM-UHFFFAOYSA-N 0.000 claims description 2
229910021380 Manganese Chloride Inorganic materials 0.000 claims description 2
GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910021446 cobalt carbonate Inorganic materials 0.000 claims description 2
ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 claims description 2
AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 claims description 2
BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 claims description 2
PFQLIVQUKOIJJD-UHFFFAOYSA-L cobalt(ii) formate Chemical compound [Co+2].[O-]C=O.[O-]C=O PFQLIVQUKOIJJD-UHFFFAOYSA-L 0.000 claims description 2
FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 claims description 2
RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 claims description 2
229940093474 manganese carbonate Drugs 0.000 claims description 2
235000006748 manganese carbonate Nutrition 0.000 claims description 2
239000011656 manganese carbonate Substances 0.000 claims description 2
235000002867 manganese chloride Nutrition 0.000 claims description 2
239000011565 manganese chloride Substances 0.000 claims description 2
229940099607 manganese chloride Drugs 0.000 claims description 2
BHVPEUGTPDJECS-UHFFFAOYSA-L manganese(2+);diformate Chemical compound [Mn+2].[O-]C=O.[O-]C=O BHVPEUGTPDJECS-UHFFFAOYSA-L 0.000 claims description 2
SGLXWMAOOWXVAM-UHFFFAOYSA-L manganese(2+);octanoate Chemical compound [Mn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O SGLXWMAOOWXVAM-UHFFFAOYSA-L 0.000 claims description 2
229910000016 manganese(II) carbonate Inorganic materials 0.000 claims description 2
XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 claims description 2
QWYFOIJABGVEFP-UHFFFAOYSA-L manganese(ii) iodide Chemical compound [Mn+2].[I-].[I-] QWYFOIJABGVEFP-UHFFFAOYSA-L 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
150000001869 cobalt compounds Chemical class 0.000 claims 5
150000002697 manganese compounds Chemical class 0.000 claims 5
REBSMYOUWCHBEY-UHFFFAOYSA-N 5-methyl-1-propan-2-yl-3-(trifluoromethyl)pyrazole Chemical compound CC(C)N1N=C(C(F)(F)F)C=C1C REBSMYOUWCHBEY-UHFFFAOYSA-N 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
150000001785 cerium compounds Chemical class 0.000 claims 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims 1
150000002816 nickel compounds Chemical class 0.000 claims 1
150000003755 zirconium compounds Chemical class 0.000 claims 1
MMDIWOSRSLNHLA-UHFFFAOYSA-N 3,5-dichloro-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=C(Cl)C(C(O)=O)=C1Cl MMDIWOSRSLNHLA-UHFFFAOYSA-N 0.000 description 6
229940074995 bromine Drugs 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 3
235000002908 manganese Nutrition 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
150000000703 Cerium Chemical class 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
159000000014 iron salts Chemical class 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
150000002642 lithium compounds Chemical class 0.000 description 2
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000002815 nickel Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
150000003754 zirconium Chemical class 0.000 description 2
CGWDABYOHPEOAD-VIFPVBQESA-N (2r)-2-[(4-fluorophenoxy)methyl]oxirane Chemical compound C1=CC(F)=CC=C1OC[C@@H]1OC1 CGWDABYOHPEOAD-VIFPVBQESA-N 0.000 description 1
WHXSMMKQMYFTQS-BJUDXGSMSA-N (6Li)Lithium Chemical compound [6Li] WHXSMMKQMYFTQS-BJUDXGSMSA-N 0.000 description 1
YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
UPPPWUOZCSMDTR-UHFFFAOYSA-N 1-methyl-pyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C=N1 UPPPWUOZCSMDTR-UHFFFAOYSA-N 0.000 description 1
YNVZDODIHZTHOZ-UHFFFAOYSA-K 2-hydroxypropanoate;iron(3+) Chemical compound [Fe+3].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O YNVZDODIHZTHOZ-UHFFFAOYSA-K 0.000 description 1
DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 1
SDYOVMHXYNKROV-UHFFFAOYSA-N 5-chloro-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=CC(C(O)=O)=C1Cl SDYOVMHXYNKROV-UHFFFAOYSA-N 0.000 description 1
XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
PLODUXQQYAOTSH-UHFFFAOYSA-N 5-tert-butylsulfanyl-3-chloro-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=C(Cl)C(C(O)=O)=C1SC(C)(C)C PLODUXQQYAOTSH-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
OAJHWYJGCSAOTQ-UHFFFAOYSA-N [Zr].CCCCCCCCO.CCCCCCCCO.CCCCCCCCO.CCCCCCCCO Chemical compound [Zr].CCCCCCCCO.CCCCCCCCO.CCCCCCCCO.CCCCCCCCO OAJHWYJGCSAOTQ-UHFFFAOYSA-N 0.000 description 1
GOKIPOOTKLLKDI-UHFFFAOYSA-N acetic acid;iron Chemical compound [Fe].CC(O)=O.CC(O)=O.CC(O)=O GOKIPOOTKLLKDI-UHFFFAOYSA-N 0.000 description 1
MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
238000006701 autoxidation reaction Methods 0.000 description 1
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
PYPNFSVOZBISQN-LNTINUHCSA-K cerium acetylacetonate Chemical compound [Ce+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O PYPNFSVOZBISQN-LNTINUHCSA-K 0.000 description 1
VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
VGBWDOLBWVJTRZ-UHFFFAOYSA-K cerium(3+);triacetate Chemical compound [Ce+3].CC([O-])=O.CC([O-])=O.CC([O-])=O VGBWDOLBWVJTRZ-UHFFFAOYSA-K 0.000 description 1
GHLITDDQOMIBFS-UHFFFAOYSA-H cerium(3+);tricarbonate Chemical compound [Ce+3].[Ce+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GHLITDDQOMIBFS-UHFFFAOYSA-H 0.000 description 1
UADULFIZHZKEOP-UHFFFAOYSA-K cerium(3+);triformate Chemical compound [Ce+3].[O-]C=O.[O-]C=O.[O-]C=O UADULFIZHZKEOP-UHFFFAOYSA-K 0.000 description 1
ZEDZJUDTPVFRNB-UHFFFAOYSA-K cerium(3+);triiodide Chemical compound I[Ce](I)I ZEDZJUDTPVFRNB-UHFFFAOYSA-K 0.000 description 1
MOOUSOJAOQPDEH-UHFFFAOYSA-K cerium(iii) bromide Chemical compound [Br-].[Br-].[Br-].[Ce+3] MOOUSOJAOQPDEH-UHFFFAOYSA-K 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229940116318 copper carbonate Drugs 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
229940076286 cupric acetate Drugs 0.000 description 1
235000019854 cupric carbonate Nutrition 0.000 description 1
239000011646 cupric carbonate Substances 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 description 1
RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 1
229940062993 ferrous oxalate Drugs 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
229910000358 iron sulfate Inorganic materials 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
PQQAOTNUALRVTE-UHFFFAOYSA-L iron(2+);diformate Chemical compound [Fe+2].[O-]C=O.[O-]C=O PQQAOTNUALRVTE-UHFFFAOYSA-L 0.000 description 1
MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
OWZIYWAUNZMLRT-UHFFFAOYSA-L iron(2+);oxalate Chemical compound [Fe+2].[O-]C(=O)C([O-])=O OWZIYWAUNZMLRT-UHFFFAOYSA-L 0.000 description 1
GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 0.000 description 1
LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
150000002611 lead compounds Chemical class 0.000 description 1
JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229940073644 nickel Drugs 0.000 description 1
229940078494 nickel acetate Drugs 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 1
HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
150000002908 osmium compounds Chemical class 0.000 description 1
IHUHXSNGMLUYES-UHFFFAOYSA-J osmium(iv) chloride Chemical compound Cl[Os](Cl)(Cl)Cl IHUHXSNGMLUYES-UHFFFAOYSA-J 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 0.000 description 1
OEERILNPOAIBKF-UHFFFAOYSA-J zirconium(4+);tetraformate Chemical compound [Zr+4].[O-]C=O.[O-]C=O.[O-]C=O.[O-]C=O OEERILNPOAIBKF-UHFFFAOYSA-J 0.000 description 1
LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

CA000604241A 1988-07-04 1989-06-28 Methode de preparation de derives de l'acide pyrazolecarboxylique Expired - Lifetime CA1337528C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP16627488		1988-07-04
JP166274/1988		1988-07-04

Publications (1)

Publication Number	Publication Date
CA1337528C true CA1337528C (fr)	1995-11-07

Family

ID=15828345

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000604241A Expired - Lifetime CA1337528C (fr)	1988-07-04	1989-06-28	Methode de preparation de derives de l'acide pyrazolecarboxylique

Country Status (13)

Country	Link
US (1)	US5053517A (fr)
EP (1)	EP0350176B1 (fr)
JP (1)	JP2743473B2 (fr)
KR (1)	KR970002871B1 (fr)
AR (1)	AR246736A1 (fr)
AT (1)	ATE127114T1 (fr)
AU (1)	AU614385B2 (fr)
BR (1)	BR8903268A (fr)
CA (1)	CA1337528C (fr)
DE (1)	DE68924011T2 (fr)
ES (1)	ES2076210T3 (fr)
GR (1)	GR3017702T3 (fr)
IL (1)	IL90665A0 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5220028A (en) *	1988-10-27	1993-06-15	Nissan Chemical Industries, Ltd.	Halogeno-4-methylpyrazoles
EP0366329B1 (fr) *	1988-10-27	1996-03-20	Nissan Chemical Industries, Limited	4-méthylpyrazoles halogénés et procédé pour les préparer
US5217523A (en) *	1989-09-23	1993-06-08	Basf Aktiengesellschaft	Pyrazole-3-carboxamides, herbicidal compositions and use
DE3931786A1 (de) *	1989-09-23	1991-04-04	Basf Ag	Pyrazol-3-carbonsaeureamide
US5532416A (en) *	1994-07-20	1996-07-02	Monsanto Company	Benzoyl derivatives and synthesis thereof
US5880290A (en) *	1994-01-31	1999-03-09	Monsanto Company	Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
US5869688A (en) *	1994-07-20	1999-02-09	Monsanto Company	Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
US5587485A (en) *	1994-07-20	1996-12-24	Monsanto Company	Heterocyclic- and carbocyclic- substituted benzoic acids and synthesis thereof
US5698708A (en) *	1996-06-20	1997-12-16	Monsanto Company	Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
US6531478B2 (en)	2000-02-24	2003-03-11	Cheryl P. Kordik	Amino pyrazole derivatives useful for the treatment of obesity and other disorders
AU1499902A (en)	2000-09-29	2002-04-08	Basf Ag	Method for producing 1 substituted 5-chloro-4 methyl pyrazoles
EP2628722A1 (fr) *	2012-02-16	2013-08-21	Bayer CropScience AG	Énaminocétones à base de CF3O et leur utilisation pour la préparation de pyrazoles à base de CF3O
CN115888385A (zh) *	2022-11-28	2023-04-04	北京科技大学	一种防止瓦斯突出的甲烷酯化剂及其制备方法和应用方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3760009A (en) *	1970-02-13	1973-09-18	Chevron Res	Hydroquinone process
US3692828A (en) *	1970-05-01	1972-09-19	Gulf Research Development Co	Process for preparing phenyl sulfone carboxylic acids
JPS5017068B1 (fr) *	1970-12-30	1975-06-18
JPS533188B2 (fr) *	1973-06-20	1978-02-03
US4623726A (en) *	1983-04-18	1986-11-18	American Cyanamid Company	Method for oxidizing alkyl groups on pyridine, quinoline and benzene ring compounds to carboxylic acids under basic conditions
DE3540839A1 (de) *	1985-11-18	1987-05-27	Bayer Ag	1-aryl-pyrazole
GB2187744B (en) *	1986-03-14	1990-01-17	Kureha Chemical Ind Co Ltd	Process for producing 2, 6-naphthalenedicarboxylic acid
DE3729598A1 (de) *	1987-09-04	1989-03-16	Hoechst Ag	Verfahren zur herstellung von 1-aryl-pyrazol-3-carbonsaeureestern

1989
- 1989-05-18 JP JP1125254A patent/JP2743473B2/ja not_active Expired - Lifetime
- 1989-06-16 US US07/367,428 patent/US5053517A/en not_active Expired - Lifetime
- 1989-06-19 IL IL90665A patent/IL90665A0/xx unknown
- 1989-06-19 ES ES89306182T patent/ES2076210T3/es not_active Expired - Lifetime
- 1989-06-19 EP EP89306182A patent/EP0350176B1/fr not_active Expired - Lifetime
- 1989-06-19 DE DE68924011T patent/DE68924011T2/de not_active Expired - Lifetime
- 1989-06-19 AT AT89306182T patent/ATE127114T1/de not_active IP Right Cessation
- 1989-06-20 AU AU36633/89A patent/AU614385B2/en not_active Expired
- 1989-06-28 CA CA000604241A patent/CA1337528C/fr not_active Expired - Lifetime
- 1989-07-03 BR BR898903268A patent/BR8903268A/pt not_active IP Right Cessation
- 1989-07-03 KR KR1019890009404A patent/KR970002871B1/ko not_active Expired - Lifetime
- 1989-07-04 AR AR89314325A patent/AR246736A1/es active
1995
- 1995-10-11 GR GR950402811T patent/GR3017702T3/el unknown

Also Published As

Publication number	Publication date
JPH02124875A (ja)	1990-05-14
EP0350176B1 (fr)	1995-08-30
GR3017702T3 (en)	1996-01-31
AR246736A1 (es)	1994-09-30
KR900001658A (ko)	1990-02-27
BR8903268A (pt)	1990-02-13
DE68924011D1 (de)	1995-10-05
AU614385B2 (en)	1991-08-29
IL90665A0 (en)	1990-01-18
DE68924011T2 (de)	1996-01-25
EP0350176A2 (fr)	1990-01-10
KR970002871B1 (ko)	1997-03-12
JP2743473B2 (ja)	1998-04-22
EP0350176A3 (fr)	1991-07-24
ES2076210T3 (es)	1995-11-01
AU3663389A (en)	1990-01-04
US5053517A (en)	1991-10-01
ATE127114T1 (de)	1995-09-15

Legal Events

Date	Code	Title	Description
2012-11-07	MKEX	Expiry

Publication	Publication Date	Title
CA1337528C (fr)	1995-11-07	Methode de preparation de derives de l'acide pyrazolecarboxylique
EP0454182B1 (fr)	1995-11-29	Dérivés de benzyléthers
CN1190961A (zh)	1998-08-19	N－取代的3－羟基吡唑类化合物的制备方法
US5202442A (en)	1993-04-13	Process for preparing pyrazolecarboxylic acid compounds
US5155258A (en)	1992-10-13	Substituted benzoic acids
JP3009515B2 (ja)	2000-02-14	３−メチルピラゾールの製造方法
SU576910A3 (ru)	1977-10-15	Способ получени производных замещенной уксусной кислоты или их солей
Castro et al.	1974	The reactions of octaethylporphyrin and its iron (II) and iron (III) complexes with free radicals
EP0772598B1 (fr)	2002-02-06	Preparation d'acides benzoiques a substitution heterocyclique et carbocyclique
GB2146983A (en)	1985-05-01	Preparation of substituted benzamides
JPS61171475A (ja)	1986-08-02	１，２，４−トリアゾ−ル−３−カルボン酸誘導体の製造方法
JPH03127784A (ja)	1991-05-30	チアゾールカルボン酸類の製造方法
JP3779615B2 (ja)	2006-05-31	５−および／または６−置換−２−ヒドロキシ安息香酸エステルの製造方法
GB2068945A (en)	1981-08-19	Process for the preparation of diphenylether carboxylic acids
Chai et al.	2001	Synthesis, structure and characterization of M Sn (M= Mo, W) bonded heterobimetallic complexes containing bis (pyrazol-1-yl) methane ligands
JP3486648B2 (ja)	2004-01-13	ピラゾールカルボン酸類の製造方法
US5342943A (en)	1994-08-30	Preparation of 1H pyrazolo [3,2-c]-S-triazole compounds
JPH06199805A (ja)	1994-07-19	３−（置換フェニル）ピラゾール誘導体の製造方法
JPH06298684A (ja)	1994-10-25	新規な４−（２−置換）フェニルベンジルブロミド類の製造法
JPS60139672A (ja)	1985-07-24	アミド誘導体の製造法
US2920102A (en)	1960-01-05	Preparation of beta-acetylvinyl esters
DE69613460T2 (de)	2001-11-22	Verfahren zur herstellung von 3-(substituiert phenyl)-5-alkyliden-1,3-oxazolidin-2,4-dion-derivaten
US5091597A (en)	1992-02-25	Manufacture of tertiary and secondary alcohols by the action of an organo-metallic compound on a compound carrying a carbonyl group
JPS6127984A (ja)	1986-02-07	ロ−ダニン酢酸誘導体
JP2893906B2 (ja)	1999-05-24	不飽和ケトン化合物の製造方法